CA2964762A1 - Methods for conversion of ethanol to functionalized lower hydrocarbons and downstream hydrocarbons - Google Patents
Methods for conversion of ethanol to functionalized lower hydrocarbons and downstream hydrocarbons Download PDFInfo
- Publication number
- CA2964762A1 CA2964762A1 CA2964762A CA2964762A CA2964762A1 CA 2964762 A1 CA2964762 A1 CA 2964762A1 CA 2964762 A CA2964762 A CA 2964762A CA 2964762 A CA2964762 A CA 2964762A CA 2964762 A1 CA2964762 A1 CA 2964762A1
- Authority
- CA
- Canada
- Prior art keywords
- ethanol
- isobutylene
- yield
- mixed oxide
- oxide catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 1183
- 238000000034 method Methods 0.000 title claims abstract description 547
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 215
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 214
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 172
- 239000003054 catalyst Substances 0.000 claims abstract description 515
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 164
- 238000004519 manufacturing process Methods 0.000 claims abstract description 92
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 46
- 239000002638 heterogeneous catalyst Substances 0.000 claims abstract description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 440
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 415
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 295
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 292
- 239000000047 product Substances 0.000 claims description 125
- 239000011572 manganese Substances 0.000 claims description 122
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 110
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 105
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 100
- 229910052799 carbon Inorganic materials 0.000 claims description 99
- 229910001868 water Inorganic materials 0.000 claims description 88
- 239000011777 magnesium Substances 0.000 claims description 85
- 239000010949 copper Substances 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 70
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 67
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 62
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- 238000000975 co-precipitation Methods 0.000 claims description 51
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- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 claims description 44
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- 229910052725 zinc Inorganic materials 0.000 claims description 41
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 claims description 40
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- 229910052726 zirconium Inorganic materials 0.000 claims description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000003208 petroleum Substances 0.000 claims description 25
- -1 zinc-aluminate Chemical compound 0.000 claims description 25
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 24
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 24
- WRFWTYGMKIUAKL-UHFFFAOYSA-N 3-methylphenol Chemical compound CC1=CC=CC(O)=C1.CC1=CC=CC(O)=C1 WRFWTYGMKIUAKL-UHFFFAOYSA-N 0.000 claims description 21
- 238000001179 sorption measurement Methods 0.000 claims description 21
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 20
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- 239000001569 carbon dioxide Substances 0.000 claims description 20
- 239000000446 fuel Substances 0.000 claims description 20
- VSSZKXRAUHZJFV-UHFFFAOYSA-N 3,5-dimethylphenol Chemical compound CC1=CC(C)=CC(O)=C1.CC1=CC(C)=CC(O)=C1 VSSZKXRAUHZJFV-UHFFFAOYSA-N 0.000 claims description 19
- 239000011135 tin Substances 0.000 claims description 19
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000005470 impregnation Methods 0.000 claims description 18
- 229910052748 manganese Inorganic materials 0.000 claims description 18
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- 239000010457 zeolite Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 16
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- 239000010795 gaseous waste Substances 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
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- 239000010936 titanium Substances 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 13
- 239000003245 coal Substances 0.000 claims description 13
- 239000003345 natural gas Substances 0.000 claims description 13
- 239000000377 silicon dioxide Substances 0.000 claims description 13
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 12
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 12
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 12
- 239000012528 membrane Substances 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
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- 230000018044 dehydration Effects 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 238000011065 in-situ storage Methods 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 11
- 150000001298 alcohols Chemical class 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052804 chromium Inorganic materials 0.000 claims description 10
- 229910052750 molybdenum Inorganic materials 0.000 claims description 10
- 229910052758 niobium Inorganic materials 0.000 claims description 10
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 10
- 239000001294 propane Substances 0.000 claims description 10
- 229910052707 ruthenium Inorganic materials 0.000 claims description 10
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 10
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- 239000002585 base Substances 0.000 claims description 9
- 229910044991 metal oxide Inorganic materials 0.000 claims description 9
- 150000004706 metal oxides Chemical class 0.000 claims description 9
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910052721 tungsten Inorganic materials 0.000 claims description 9
- 229910052684 Cerium Inorganic materials 0.000 claims description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052793 cadmium Inorganic materials 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 8
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 8
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- 229910052735 hafnium Inorganic materials 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
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- 238000000926 separation method Methods 0.000 claims description 8
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
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- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 6
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- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/06—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of zinc, cadmium or mercury
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
- B01J37/082—Decomposition and pyrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
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- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
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- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
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- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
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- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/32—Manganese, technetium or rhenium
- C07C2523/34—Manganese
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- C10L2200/00—Components of fuel compositions
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- C10L2270/00—Specifically adapted fuels
- C10L2270/04—Specifically adapted fuels for turbines, planes, power generation
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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- Y02P20/10—Process efficiency
- Y02P20/129—Energy recovery, e.g. by cogeneration, H2recovery or pressure recovery turbines
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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| PCT/US2015/055581 WO2016061262A1 (en) | 2014-10-14 | 2015-10-14 | Methods for conversion of ethanol to functionalized lower hydrocarbons and downstream hydrocarbons |
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| MX2017004996A (es) | 2014-10-14 | 2017-12-12 | Gevo Inc | Metodos para conversion de etanol a hidrocarburos inferiores funcionalizados e hidrocarburos de corriente abajo. |
| US10010870B2 (en) | 2015-11-12 | 2018-07-03 | Saudi Arabian Oil Company | Synthesis of catalytic materials for metathesis and isomerization reactions and other catalytic applications via well controlled aerosol processing |
| US9969621B2 (en) | 2016-05-04 | 2018-05-15 | Saudi Arabian Oil Company | Methods for processing fumed metallic oxides |
| RU2656602C1 (ru) * | 2017-03-31 | 2018-06-06 | Общество с ограниченной ответственностью "ЭТБ каталитические технологии" (ООО "ЭТБ КаТ") | Одностадийный способ получения бутадиена |
| JP2020531255A (ja) | 2017-08-17 | 2020-11-05 | サウジ アラビアン オイル カンパニーＳａｕｄｉ Ａｒａｂｉａｎ Ｏｉｌ Ｃｏｍｐａｎｙ | 触媒を発生させるための表面種の制御されたコーティングのためのエアロゾル処理方法 |
| CN109745988B (zh) * | 2017-11-08 | 2022-03-01 | 中国石油天然气股份有限公司 | Cu基水煤气变换反应催化剂的制备方法 |
| CN111936452B (zh) * | 2018-01-04 | 2024-05-03 | 吉沃公司 | 经非均相催化剂将杂醇油混合物改质为更高价值的可再生化学品 |
| US11369950B2 (en) | 2018-02-21 | 2022-06-28 | Saudi Arabian Oil Company | Multi-functional composite catalyst materials and methods of synthesizing the catalyst materials |
| US11180609B2 (en) | 2018-08-02 | 2021-11-23 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
| US11033892B2 (en) | 2019-01-24 | 2021-06-15 | Saudi Arabian Oil Company | Methods for reacting chemical streams with catalysts comprising silica, alumina, and tungsten |
| BR112022003092A2 (pt) | 2019-08-21 | 2022-08-09 | Gevo Inc | Melhoramento de óleos fúseis sobre alumina dopada |
| CN111790437B (zh) * | 2020-07-15 | 2022-09-20 | 陕西延长石油（集团）有限责任公司 | 一种液相法乙醇制备2-戊酮的锶-钽-钛三金属氧化物催化剂及其制备方法与应用 |
| CN112044450B (zh) * | 2020-07-17 | 2021-06-15 | 昆明理工大学 | 一种酸碱双功能生物质碳基催化剂及其制备方法 |
| BR102020020883A2 (pt) | 2020-10-09 | 2022-04-26 | Petróleo Brasileiro S.A. - Petrobras | Processo para produção de querosene de aviação renovável |
| BR102021018172A2 (pt) * | 2021-09-13 | 2023-03-28 | Petróleo Brasileiro S.A. - Petrobras | Método de preparo do catalisador para produção de butadieno a partir do etanol em uma etapa, catalisador e uso |
| US20240117149A1 (en) | 2022-09-28 | 2024-04-11 | The Goodyear Tire & Rubber Company | Rubber - forming additives from end of life tires through syngas production |
| US20240124683A1 (en) | 2022-09-28 | 2024-04-18 | The Goodyear Tire & Rubber Company | Rubber - forming additives from biomass through syngas production |
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| US2931787A (en) * | 1955-02-18 | 1960-04-05 | Consolidation Coal Co | Method for recovering purified phenolic isomers from low boiling cresylic acids |
| US2984644A (en) | 1957-08-26 | 1961-05-16 | Phillips Petroleum Co | Butyl rubber/heterocyclic nitrogen base rubber blend |
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| US3998755A (en) * | 1971-05-03 | 1976-12-21 | Universal Oil Products Company | Regeneration of a coke-deactivated, acidic bimetallic Pt-1r catalyst |
| FR2142268A5 (de) * | 1971-06-18 | 1973-01-26 | Petroles Cie Francaise | |
| US3803249A (en) * | 1972-04-12 | 1974-04-09 | Atlantic Richfield Co | Vapor phase conversion of acetone to 3,5-xylenol in a single stage |
| FR2342263A1 (fr) | 1976-02-27 | 1977-09-23 | Raffinage Cie Francaise | Procede d'obtention d'isobutylene d'une purete superieure a 99,5 % en poids |
| CA1320735C (en) * | 1987-11-24 | 1993-07-27 | Ramakrishnan Ramachandran | Process for the production of nitriles and anhydrides |
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| US5210329A (en) | 1992-02-18 | 1993-05-11 | General Electric Company | Process for preparing bisphenol-A |
| JP3189858B2 (ja) | 1992-11-16 | 2001-07-16 | 三菱瓦斯化学株式会社 | メタクリル酸メチルの製造法 |
| US5393918A (en) | 1993-12-02 | 1995-02-28 | Rohm And Haas Company | High yield process for the production of methacrylic acid esters |
| US5434316A (en) | 1994-07-28 | 1995-07-18 | General Electric Company | Purification of bisphenol-A |
| US5567853A (en) * | 1995-02-17 | 1996-10-22 | Arco Chemical Technology, L.P. | Purification of acetone |
| WO1997012654A1 (en) * | 1995-10-05 | 1997-04-10 | Exxon Chemical Patents Inc. | Method for recovering acetone |
| US5786522A (en) | 1996-09-13 | 1998-07-28 | General Electric Company | Manufacture of bisphenol-A |
| EP1186592A1 (de) | 2000-09-11 | 2002-03-13 | Mitsubishi Gas Chemical Company, Ltd. | Herstellung von Methacrylaten |
| MXPA02011489A (es) * | 2001-12-04 | 2003-06-30 | Rohm & Haas | Procesos mejorados para la preparacion de olefinas, acidos carboxilicos insaturados y nitrilos insaturados, a partir de alcanos. |
| DE60239222D1 (de) | 2001-12-21 | 2011-03-31 | Asahi Kasei Chemicals Corp | Oxidkatalysatorzusammensetzung |
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| JP2005253415A (ja) | 2004-03-15 | 2005-09-22 | Rikkyo Gakuin | 天然芝構造体の管理システム、天然芝構造体及びコンピュータプログラム |
| WO2008024109A1 (en) * | 2006-08-22 | 2008-02-28 | Shelfer Jr Bennett H | Process and apparatus for commercially producing motor fuel-grade ethanol |
| JP2011505490A (ja) | 2007-12-03 | 2011-02-24 | ジーヴォ，インコーポレイテッド | 再生可能組成物 |
| US8193402B2 (en) | 2007-12-03 | 2012-06-05 | Gevo, Inc. | Renewable compositions |
| WO2010064652A1 (ja) * | 2008-12-03 | 2010-06-10 | 国立大学法人 北海道大学 | アセトンからイソブチレンを製造する方法 |
| US20100150805A1 (en) * | 2008-12-17 | 2010-06-17 | Uop Llc | Highly stable and refractory materials used as catalyst supports |
| JP2012518658A (ja) | 2009-02-24 | 2012-08-16 | ジーヴォ，インコーポレイテッド | 再生可能なブタジエンおよび再生可能なイソプレンの製造方法 |
| US20110087000A1 (en) | 2009-10-06 | 2011-04-14 | Gevo, Inc. | Integrated Process to Selectively Convert Renewable Isobutanol to P-Xylene |
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| EP2566830B1 (de) | 2010-05-07 | 2017-03-22 | GEVO, Inc. | Erneuerbares düsenkraftstoff-rohmaterial aus isobutanol |
| WO2012061372A1 (en) | 2010-11-01 | 2012-05-10 | Gevo, Inc. | Renewable xylenes produced from biological c4 and c5 molecules |
| US8975452B2 (en) * | 2012-03-28 | 2015-03-10 | Celanese International Corporation | Process for producing ethanol by hydrocarbon oxidation and hydrogenation or hydration |
| MX2014013321A (es) * | 2012-05-04 | 2015-02-10 | Butamax Advanced Biofuels Llc | Procesos y sistemas para la produccion y recuperacion de alcohol. |
| WO2014070354A1 (en) | 2012-10-31 | 2014-05-08 | Washington State University | Stable mixed oxide catalysts for direct conversion of ethanol to isobutene and process for making |
| MX2017004996A (es) | 2014-10-14 | 2017-12-12 | Gevo Inc | Metodos para conversion de etanol a hidrocarburos inferiores funcionalizados e hidrocarburos de corriente abajo. |
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| EP3207004A4 (de) | 2018-05-30 |
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